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Issue 25, 2019
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Simple NMR predictors of catalytic hydrogenation activity for [Rh(cod)Cl(NHC)] complexes featuring fluorinated NHC ligands

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Abstract

A series of imidazolium salts precursors for N-heterocyclic carbenes (NHCs) featuring fluoroaryl substituents have been prepared along with their selenides and rhodium complexes. Tests of the catalytic activity of the [Rh(cod)Cl(NHC)] complexes in the transfer hydrogenation of acetophenone with iPrOH shows that the rhodium complexes bearing fluorinated NHCs are better than their non-fluorinated counterparts. The order of activity being 4-F-C6H4 < 2,4-F2-C6H3 < 2,4,5-F3-C6H2 < 2,6-F2-C6H3 < 2,4,6-F3-C6H2. This order of reactivity is consistent with a number of simple NMR measures of the electronic properties of these systems, including 1JCH of the NHC·HBF4 salts, δ(77Se) of the NHC selenides and 1JRh–C and δ(13Ccarbene) of the [Rh(cod)Cl(NHC)] complexes.

Graphical abstract: Simple NMR predictors of catalytic hydrogenation activity for [Rh(cod)Cl(NHC)] complexes featuring fluorinated NHC ligands

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Supplementary files

Article information


Submitted
21 Mar 2019
Accepted
28 May 2019
First published
30 May 2019

Dalton Trans., 2019,48, 9317-9327
Article type
Paper

Simple NMR predictors of catalytic hydrogenation activity for [Rh(cod)Cl(NHC)] complexes featuring fluorinated NHC ligands

M. S. S. Jamil, S. Alkaabi and A. K. Brisdon, Dalton Trans., 2019, 48, 9317
DOI: 10.1039/C9DT01219B

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